Lies That Chelsea Handler Told Me Part 10

The one thing that has been consistent about Chelsea Handler since the day I met her is that she is painfully honest. She will tell you the truth, even if you don't want to hear it, anytime she feels it needs to be said.

At the same time, you can't believe a f.u.c.king word she says.

Crazy combo, right? She is one of the truest, most loyal friends you could ever hope to have in your lifetime, but if the window is cracked open even a bit for her to f.u.c.k with you, she will say and make you believe anything so she can have a good laugh.

That's harder to handle than you would think. Luckily, I was prepared. I grew up with three older brothers who waged mental warfare on me for my entire childhood. They had me convinced for years that I was adopted but that my parents would never admit it because they didn't want to hurt my feelings. They said that if I talked to our parents about it, my mom would most likely kill herself. Not wanting to be responsible for my mom's untimely demise, I resisted the temptation.

After a while, I suspected they were lying. There were pictures of me all over the house, and my brothers and I kind of looked the same, but every time my mom or dad yelled at me, my oldest brother would be sure to tell me that they were harder on me because "I wasn't blood." It wasn't until I heard my grandmother talking about how she was at the house when my parents brought me home from the hospital that I was able to put the final pieces of the puzzle together.

"I knew it! I knew I wasn't adopted!" I shot up and screamed. Everybody just stared at me. They had no f.u.c.king idea what I was talking about. s.h.i.t, my brother barely remembered. He hadn't teased me about it in years. I was eleven years old. Since then, I have learned to take everything anyone says with a grain of salt. Especially a.s.sholes like Chelsea Handler.

My wife does not.

My wife, Beth, is an extremely intelligent woman. She's a writer and director whose films have won awards all over the world. She also might be the single nicest person on the face of the earth, someone who always comes from a place of truth and who takes what people say at face value because that's how she treats people in return. Unfortunately, all of those amazing traits also make her very susceptible to practical jokes.

How did she end up with an a.s.shole like me? No idea.

My wife, Beth, and Chelsea in NYC. My wife, Beth, and Chelsea in NYC.

Sometimes I feel bad bringing her around my j.e.r.k.-.o.f.f. friends because we are all such a.s.sholes. Our idea of fun is hurling insults at one another and pulling pranks that have a good possibility to humiliate. So when I started bringing her around Chelsea and the gang, I thought, This might get ugly. This might get ugly.

Things were fine for a while, until one day when we were all hanging out at Chelsea's and somebody brought up the Lakers. As soon as Chelsea heard the word Lakers Lakers, she said, "Oh yeah, I just won fifty thousand dollars on that game last night." This is her thing. Whenever someone brings up a sports team, she talks about how much money she won on a game they played in. Every single time.

My wife then said, "Fifty thousand dollars? Oh my G.o.d, Chelsea. That's amazing."

And that's when Chelsea smelled blood.

Let me say, first of all, that Chelsea Handler does not know one thing about sports. Totally r.e.t.a.r.ded. Wait, I take that back, she knows one one thing: the 1986 New York Mets. And I have to admit, she's kind of a genius the way she uses them. Since it's the only sports team she knows anything about, she brings it up in any sports-related conversation to make people think that she has a clue. She doesn't. thing: the 1986 New York Mets. And I have to admit, she's kind of a genius the way she uses them. Since it's the only sports team she knows anything about, she brings it up in any sports-related conversation to make people think that she has a clue. She doesn't.

I picked up on this one day when I heard her reference the team for the one hundredth time. I said to her, "You don't know s.h.i.t about sports, do you?"

She said, "Of course, I do. Didn't you just hear what I said about the Mets?"

"That's the only team you ever talk about when people bring up sports."

Beat. Chelsea then walked away in her usual style-pretending to text. This is what she does when she's been caught at a lie and doesn't have the energy to maintain it. There is no way a person texts as much as Chelsea pretends to. It is just one more way for her to ignore and hide from the people she so often disappoints.

So when Chelsea realized that there was someone in the mix who didn't know that she was full of s.h.i.t, she went in for the kill. She told my wife at a party that she'd won more than five hundred thousand dollars the year before gambling and that she bet on games every weekend.

"That's incredible," Beth said. "So, do you bet on everything?"

"Pretty much," Chelsea said. "I call my bookie once or twice a week. Last year I won so much that for tax purposes, I had to hide half a million dollars under my mattress. My business manager had me sit out last football season and I had to miss the play-offs. I'd never been more irate in my life."

I really believe that when Chelsea spins stories like this, she's almost waiting for you to call "bulls.h.i.t." She pushes and pushes, expecting you at some point to tell her that she's full of c.r.a.p and then she just moves on to the next target.

Back to that evening at Chelsea's house. After Beth believed her story about winning fifty thousand bucks, Chelsea got up and walked away, asking if anyone needed a drink. This was when my wife looked at me with her eyes as big as quarters and said, "Is that true?"

She turned to me to tell her the truth. She turned to me to lead her down the right path. She turned to me, and do you know what I said?

"Absolutely."

f.u.c.k. Wait, what did I just say? Did I really just say "absolutely"? What was I thinking? I'll tell you what I was thinking, and it's an answer I think I gave a little earlier.

I'm an a.s.shole.

Look, I love my wife-have her name tattooed on my finger-but I just couldn't help myself. It was instinct. And I know some of you are thinking, It's your instinct to lie? It's your instinct to lie? No, that's not it at all, and that's what makes people like me different. The instinct isn't to lie; it's to f.u.c.k with people. Whenever we have Thanksgiving and all of my brothers are around, one of us always puts a plate in the oven for a long time, takes it out, and leaves it on the counter. Why? Because someone always picks it up, burns their hand, and drops it to the ground. It happens every year and it's funny every time. Is this male humor? Of course. Most women wouldn't find this entertaining in the least, but Chelsea would, and do you know why? Because Chelsea is a man. A man with really big t.i.ts. No, that's not it at all, and that's what makes people like me different. The instinct isn't to lie; it's to f.u.c.k with people. Whenever we have Thanksgiving and all of my brothers are around, one of us always puts a plate in the oven for a long time, takes it out, and leaves it on the counter. Why? Because someone always picks it up, burns their hand, and drops it to the ground. It happens every year and it's funny every time. Is this male humor? Of course. Most women wouldn't find this entertaining in the least, but Chelsea would, and do you know why? Because Chelsea is a man. A man with really big t.i.ts.

Go for the joke and then let s.h.i.t sort itself out afterward. Not always a great trait but, at the very least, it's entertaining.

By the end of the evening, I had almost forgotten about Chelsea's story. Since the joke had no real payoff, no big "Ha-ha! Joke's on you!" ending, I figured that it would just eventually fade away. I was wrong.

Two things I underestimated: Beth's sudden interest in gambling and Chelsea's love of f.u.c.king with people.

In the house I grew up in, for a prank to be worth it, there had to be a big payoff. Someone believing that you were a gambler when you weren't wouldn't have been enough. You would have had to make the other person bet and lose a s.h.i.tload of cash or pretend to be in debt and hire fake mobsters to come over to the house to collect. Something where there were real consequences or you scared the living s.h.i.t out of the other person.

But Chelsea is unique. The joy she gets out of even the little things puts her in a cla.s.s all her own. Even if she has you believing something for only five seconds, it's fine with her. You can tell someone is truly into practical jokes if they don't need to be there when the payoff happens. Just the knowledge that it's going to happen is enough for Chelsea.

Then came our trip to the Bahamas. Chelsea chartered a ridiculous yacht for a group of people for three days. I couldn't have been more excited about the trip, and didn't consider for a second that Chelsea would use this as an opportunity to destroy my marriage. Every opportunity she had, she talked to Beth about gambling. How much she was winning, how easy it was for her, how she almost felt bad about "the gift" she had been given, blah, blah, blah. I had to walk away when I heard Chelsea say to Beth, "What's so crazy about all this is that I have so much good fortune already with the show and my books, and my tour, and then on top of that the universe rewards me with winning almost every bet I make on sports? Obviously someone upstairs is looking out for me." I couldn't f.u.c.king believe what I was hearing.

I had dug myself a bit of a hole.

If I had told my wife then, in the middle of paradise, at the apex of the nicest, most lavish weekend the two of us had ever been able to spend together, things would have gone downhill very quickly. The questions would have come at me fast and furious. "Why would you do that to me? What else do you lie to me about? How could you choose a joke over your wife?" All valid questions, none of which I had an answer to. I was screwed. You know who wasn't?

Chelsea.

It wasn't her responsibility to tell Beth the truth; it was mine. I've known Chelsea for ten years, and I've seen her pull her nonsense over and over. I've seen her persuade a drunk friend of mine whom she'd never met make a toast to a family member of mine he'd never met. I've seen her convince a driver in Cincinnati that she was in labor but absolutely needed to get some chicken nuggets from Wendy's before he dropped us off at the hotel, which-she also convinced him-had a pediatric unit. I've seen her convince a child that instead of being able to house children in her womb, she is able to house parakeets and certain reptiles.

It's usually hilarious to watch when it doesn't involve you or a loved one. Chelsea has this amazing way of enlisting you in her army. Partly because we love practical jokes and partly because you think that if you're in on it, you can't be the b.u.t.t of it.

In the Bahamas, she was nonstop. Not just with Beth but with everyone. Her love of the five-second joke was evident all day every day. I can't remember the last time I laughed as hard as when she sprayed half a bottle of suntan lotion on someone's face and then had him stay still for pictures.

This is Geof Wills, who runs Chelsea's stand-up tours. He's the only person I know who's more immature than Chelsea. This is Geof Wills, who runs Chelsea's stand-up tours. He's the only person I know who's more immature than Chelsea.

This is Geof minus the lotion and minus the shirt. Chelsea brings him on vacations all the time just so she can photograph him with his shirt off and yell, "Watch out, fish!" every time he enters the water. This is Geof minus the lotion and minus the shirt. Chelsea brings him on vacations all the time just so she can photograph him with his shirt off and yell, "Watch out, fish!" every time he enters the water.

And remember the 1986 Mets? Well, one day we were going along the coast in a fishing boat when she started to tell everyone that all of the houses on that stretch of the beach were bought by the members of the 1986 Mets. She pointed to the houses and said things like "That's Darryl Strawberry's house, that's Doc Gooden's..." And people were all into it. They asked questions: "Why did they buy all of these houses down here?" "Did they really make that much money?"

"Of course they did," Chelsea said. "You don't win a World Series like that and not get hooked up with major endors.e.m.e.nt money. Mookie Wilson has the biggest one. A lot of people don't know that he had the biggest contract." Her own agent, who is a huge sports fan, was sitting there staring at all the houses on the sh.o.r.eline she was pointing at with his mouth gaping open like a Special Olympics champion.

Again, no huge payoff but enough to feed the beast. She delivered each line of bulls.h.i.t like she was reading it out of the 1986 New York Mets Book of Facts 1986 New York Mets Book of Facts. She kept so many b.a.l.l.s in the air that I couldn't imagine how she remembered all of them. She's very savant-like when she spews her nonsense. She rattles lies off so quickly and matter-of-factly that the people who have to gulp them up are usually so impressed by her knowledge they more often than not end up thanking her. That's the biggest joke of all.

There happened to be a horse race coming up, the Preakness, that my wife really wanted to bet on. She's from Louisiana and there was a Cajun jockey who would be racing. Between the nostalgic feelings she had about her home state and Chelsea's "incredible" sports knowledge, Beth figured it was a sure thing. The entire weekend on the boat she and Chelsea talked about it and decided that when we got to New York they would place the bet.

Chelsea kissing my wife in the Bahamas. I am in the background laughing at her baseball stats. You can see the evil look in Chelsea's eyes. Chelsea kissing my wife in the Bahamas. I am in the background laughing at her baseball stats. You can see the evil look in Chelsea's eyes.

I had to figure out a way not to lose this money. The two of them combined knew as much about horse racing as I do about tile flooring. (I'm a Jew.) As the horse race got closer, I did get a little lucky.

We were in New York for my performance at Radio City Music Hall. I think Chelsea performed that night, too, but I'm not 100 percent sure on that. The race was happening during the time we were all getting ready for the show and Chelsea was not (thank the Lord) answering her phone. Beth said she was going to place her bet anyway.

"Are you sure you wanna do that without talking to Chelsea?" I asked.

"Yup," she said. "I know how I want to bet and I'm just going to set up an online account."

"Huh?"

"I've been reading about it and there are lots of places I can just lay my bet online."

I was f.u.c.ked. As I mentioned, my wife is a director, which means she researches s.h.i.t. When she's into something, she wants to know everything there is to know on that subject. And her current subject was, unfortunately, betting. We had a bigger problem than I thought.

I had to figure a way out of this. Wait, I know Wait, I know, I thought. How about I do something stupid like tell another lie? How about I do something stupid like tell another lie? r.e.t.a.r.d. r.e.t.a.r.d.

"Honey, why don't you go take a shower so you aren't rushed to get ready and I'll set up your account and place the bet."

"Uh... are you sure?"

She was nervous for two reasons. One, I am a technological idiot. Don't know how to do anything with computers at all. Besides p.o.r.n and ESPN.com, the Interweb is like a foreign language to me. The second reason she was nervous was that I always break electronics. I don't have a metal plate in my head or anything, but there is something in my body that f.u.c.ks s.h.i.t up. My cell phone crashes all the time, remotes break, brand-new DVD players stop working, and, most of all, laptops s.h.i.t the bed. This time, I would just claim that it had happened again and there was no way to set up the account.

"I can do it," I said. "Just take your shower."

"Okay, but hurry. There's only fifteen minutes until the race starts."

Perfect.

So while she was in the shower I sat there, watched TV, and right when I heard the water stop, yelled, "What is going on?" and took the battery out of the computer.

Beth came out of the bathroom in a towel. "What's wrong?"

I told her that the computer had just stopped working. She came over, tried to turn it on, and said, "I knew I should have done it myself."

And with that, she went into the other room to get ready for the show and watch the race. She didn't yell and she didn't make any snide comments, but I knew she was angry. That's how nice she is. I figured she'd be angry right up until the race ended, and when her horse lost she would thank me for being too stupid to work a computer and realize that gambling just wasn't for her.

And then the race started.

And then her horse won.

Big time.

And then she came storming out of the room.

And then my phone rang.

It was Chelsea. "Can I talk to Beth?"

"No."

"Is that Chelsea?" Beth said. "Let me talk to her. Give me the phone! h.e.l.lo? I know. I can't believe it! No, I didn't because Josh broke the computer... We did call but n.o.body answered... How much? You won $200,000?" Beth's face dropped, but she managed to muster a "That's unbelievable! I can't believe I missed out on it either!" she said, glaring at me again. "Okay, see you tonight."

I apologized profusely to my wife, but she just stared into s.p.a.ce for a few minutes. "I would've won five thousand dollars, Josh. Dammit."

Not only did I feel awful, but I was starting to feel a little Black Swan Black Swan-y. My mind was racing back and forth trying to distinguish fact from fiction. I couldn't grasp if my wife would truly have won the money or if Chelsea was rigging sporting events all across the globe. I kept reminding myself of what was real and what wasn't, but eventually I had to sit down. When we were both able to pull ourselves together, we met Chelsea at a Belvedere event she had to go to that night.

She and Beth made plans to bet on an upcoming horse race, and I had no credibility to stop it because if I had actually set up the account, Beth would have won. The thing is, I knew I had to stop her, because I am a gambler. I lose money every weekend during football season, and the one thing I know is, no matter how "prepared" you think you are, no matter how much you research the games, you're gonna lose. Problem with that? The more knowledgeable you are about the sport, the more you chase your money. Don't believe me? Ask my bookie or the Las Vegas casinos that seem to spring up quicker than herpes at a Chelsea Lately Chelsea Lately staff off site. staff off site.

The only way to stop it was to tell Beth the truth, which was gonna suck nuts for me. I was completely at fault. I hadn't stopped the joke because I'd figured it would stop itself, but, no, it had just kept spiraling and spiraling. She was gonna be p.i.s.sed, and rightly so. I had allowed her to be led astray for weeks and had never said anything. I had betrayed her trust. But what was I supposed to do? Wait until she lost money and then tell her about the joke? There was gonna be a fight. A big one. The worst kind of fight, mind you; the kind I couldn't win.

I decided to wait until the end of the week and then take her on a nice weekend to Santa Barbara. I figured that sometime on the drive up there, she would forgive me because I'm a dumba.s.s and the weekend together would just put a bow on it. I told Chelsea that I was going to tell Beth about the joke and maybe to expect a tiny little s.h.i.t storm, but nothing too bad.

When Friday came, I told Beth I needed to talk to her, but she said she really needed to tell me something first. Knowing that I was delivering nothing she wanted to hear, I decided I should probably build up as much goodwill as I could, so I let her do the honors.

"I lost ten thousand dollars," she said.

Uh... what? I'm sorry, it sounded like you said you lost ten thousand dollars, but I know there's no way that's possible, because we don't have ten thousand dollars for you to lose. I know some of you are thinking, "What do you mean you don't have ten thousand dollars to lose? That's nothing. You're on TV and rich." One of those is true. Let's just say that with a lot of my checks, after I pay The Man, my agent, lawyer, and manager, I barely have enough left over to get drunk. But make no mistake: ten thousand dollars is a lot of f.u.c.king money.

"I don't understand," I said. "How did you lose ten thousand dollars?"

"Well, Chelsea and I bet on a basketball game last week and won." What? They bet a basketball game last week? How did I not know about that? "We bet one more Monday and won." What in the f.u.c.k is going on here? "So, I thought I would try one on my own, and I lost. I'm so sorry, baby. I don't know what I was thinking. I was winning. It all seemed so easy, like I could never lose."

Oh. My. G.o.d. This was not the conversation I thought I I was going to have. Ten thousand dollars? was going to have. Ten thousand dollars?

I called Chelsea. "Beth lost ten thousand dollars."

Silence.

"Did you hear what I said?"

"I heard you," she responded. "That's not good."

"No s.h.i.t that's not good. Why were you guys gambling?"

"Well, every fake bet I made I would have won, so I thought I'd try a couple of real ones," she explained. "Beth kept calling and calling about when we were betting, so I let her bet with me. Ten thousand dollars. Wow. That's a lot of money. I'll call you back."

Fifteen minutes later I got this text: It's not $10K. It's $15K. His name is Trent. 310-x.x.x-x.x.xx. I'm really sorry about this."

Great. Fifteen thousand I didn't have that I needed to sh.e.l.l over to a bookie. So I called him. I figured I could explain the situation and tell him that I'd pay it off in two installments. Now, I've been around enough bookies to know that normally there's no way they would let that happen, but I figured I would drop Chelsea's name and the guy would cut me some slack. I'll cut right to the only quote you need to know from that conversation.

"I don't care if you're friends with the Pope. It's fifteen K all at the same time."

There was no getting out of this. Fifteen thousand dollars basically would wipe out my little cushion. But as much as we couldn't afford to pay this guy, we had to pay this guy. Trent didn't strike me as a dude who was going to let $15K just walk away. The next day, I set up a time to go over to his house and then went to the bank to get the money.

You ever write a check big enough for you not to want to let go of it? Imagine that... but with cash. I had fifteen thousand dollars in cash in my hand. I'd be lying if I told you the idea of driving to Mexico and seeing how long I could be drunk off $15K didn't at least flash through my mind. And by flash, I mean I thought about it for about twenty-five minutes.